1. Field of the Invention
This invention relates to novel chemical compounds useful as silver halide complexing agents, to novel intermediates useful in the synthesis of said compounds and to processes for the preparation thereof.
2. Description of the Prior Art
The protection of carbonyl groups during synthesis is well-known, and the importance of ethylene thioketal and hemithioketal (or -acetal) protecting groups in steroid chemistry has been discussed by L. F. Fieser and M. Fieser, Steroids, Reinhold, 1959, pp. 307-310 and C. Djerassi, Steroid Reactions, Holden-Day, 1963, pp. 21-34.
Recently, D. W. Emerson and H. Wynberg. Tetrahedron Letters, 1971, p. 3445 and W. F. J. Huurdman, H. Wynberg and D. W. Emerson, ibid., 1971, p. 3449 reported the facile cleavage of 2-substituted 1,3-dithianes and related compounds with N-chloro-p-toluenesulfonamide sodium salt (Chloroamine-T) under mild conditions, thus making these systems useful as carbonyl protecting functions. It has been postulated by D. W. Emerson and H. Wynberg that the mono-N-tosylsulfimides of various 2-alkyl substituted dithio and oxathio heterocycles open to produce a stabilized carbonium ion which subsequently undergoes fragmentation leading to a carbonyl compound.
In one aspect, the present invention is concerned with this reaction as applied to 1,3-dithianes and related compounds that are unsubstituted in the 2-position, and in another aspect is concerned with the oxidation and oxidation products of the mono-N-tosylsulfimides produced by the aforementioned reaction of N-chloro-p-toluenesulfonamide sodium salt with 2-unsubstituted dithiocycloalkanes. In addition, this invention is concerned with imino cleavage products of the oxidized compounds and derivatives thereof and with certain thioether-substituted compounds derived from these compounds.